


First Times Are Always Awkward

by DeadlyMidnightshade



Category: Dear Evan Hansen - Pasek & Paul/Levenson
Genre: Alternate Universe - Canon Divergence, Alternate Universe - Everyone Lives/Nobody Dies, Anal Sex, Bottom Evan, Connor Deserves Happiness, Connor had scars, Connor never saw Evan's letter, Established Relationship, Evan is too cute for his own good, First Time, Fluff and Smut, Gay, Heidi is a good mom, Insecurity, M/M, Sassy Evan, Scars, Top Connor, Tree bros for life, cause this fandom needs more of both, evan is a nervous nelly, it's all gay
Language: English
Status: Completed
Published: 2017-07-11
Updated: 2017-07-11
Packaged: 2018-11-30 18:40:29
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,872
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11469399
Author URL: https://archiveofourown.org/users/DeadlyMidnightshade/pseuds/DeadlyMidnightshade
Summary: Evan sucked in a deep breath. He stared into the mirror. “Dear Evan Hansen, today- no, tonight, it’s night. Tonight is going to be a good night because you’re going out with Connor and,” Evan sucked in a breath and quickly spat out, “You’regoingtoaskforsex!”





	First Times Are Always Awkward

**Author's Note:**

> I did a Be More Chill fic so I obviously have to do a Dear Evan Hansen one. It's like a law, or something.

 

Evan combed through his hair and tried to straighten out his shirt. It was a lot easier to get ready without the cast on his arm. His eyes locked with the mirror. He could do this. All he had to do was ask. Evan whined but shook off the anxious feeling. He could do this!

Evan sucked in a deep breath. He stared into the mirror. “Dear Evan Hansen, today- no, tonight, it’s night. Tonight is going to be a good night because you’re going out with Connor and,” Evan sucked in a breath and quickly spat out, “You’regoingtoaskforsex!”

He exhaled. He had said sex out loud, good first step.  Evan heard his phone buzz.

_Connor: On my way_

Evan shook off his remaining jitters and left the room. He had done everything on his checklist. Washed, brushed teeth, washed, shaved, washed, contemplated on how to crawl in a hole and die if this didn’t work out. He had done all the essential things. He grabbed a messenger bag and put a change of clothes in it, just in case. The teen looked around and checked his mirror one more time. That was a mistake, now he felt even more insecure. Evan ran out of the room before his nerve left him.

Heidi was waiting for him at the bottom of the stairs. He really didn’t give his mother the credit she deserved. She was the one that helped him when he had questions about sex.

Heidi beamed at the site of her son. “Oh, don’t you just look handsome!” She held up a bag for him. "Here, you’ll need these.”

Evan quirked and eyebrow and looked in the bag. “Whydidyoubuysomanycondoms?!” Evan screech, face red and completely embarrassed.

Heidi merely shrugged, “I didn’t know his size.”

Evan felt like his earlier planning of crawling into a hole was going to be useful. He nevertheless thanked her for the condoms and bottle of lube he now realized was in there. Evan tied the plastic bag and put it in his satchel before securing it shut. He did not want anything flying out unexpectedly.

“Be confident,” Heidi advised before adding, “and be safe.”

Evan nodded and gave his mom a kiss on the cheek. “I-I will.”

A knock at the door shocked both of them.

Evan sucked in a breath before going to open it. He looked up at Connor. The other teen was on his baggy jacket and some ripped jeans. The smile he wore made Evan’s heart melt. “Hey Evangreen.”

“H-hi,” Evan stammered out. It wasn’t like it was their first date, though that had started and ended awkwardly too. Actually, all of it had been awkward. Evan eyes widened. He forgot to brush his teeth again. “W-wait here, IforgotsomethingandI’llberightback!”

Connor had no idea how Evan could talk so damn fast. “He should take up rapping.”

Heidi chuckled at that. “Maybe he’ll be the next Eminem.” She turned to Connor, “How have you been?” she asked with a sweet smile.

Connor always felt like she was a true mom. A type of mom that he had only seen on TV or read about in books. The kind that loved their kid to death and would do anything for them. “Good,” Connor answered, and for once it was genuine. He’d been really good. He’d never admit it, but pushing Evan had led to one of the best things in his life.

Heidi frowned, “How has _he_ been?”

Connor frowned too. He didn’t like talking about Evan behind his back, but there was nothing bad to say. “He’s been fine, stutters, but it’s really too cute and I won’t stop him.” 

Heidi beamed. “That’s wonderful, Connor. You two are just what the other needed.”

Connor chuckled. _Yeah, that and intense therapy_ , he thought. Evan’s footsteps made him straighten up a bit.

“Sorry, sorry,” he mumbled and moved to Connor. “Let’s um… let’s go.”

Connor noticed his face was flushed. He wondered what the hell Evan had done up there.

“If you come back here and I’m gone, don’t worry. I have to work tonight,” Heidi said.

Connor nodded. “I’ll bring him back in one piece, maybe,” he teased, which made Evan’s face turn beet red.

“Connor!” the other squeaked, “let’s go!”

The taller teen chuckled and followed his boyfriend to the car. “What’s up with you?” he asked. “I haven’t seen you this jittery since our first date.”

Evan groaned. “Don’t remind me.”

“I thought it was a good first date.” Connor opened the car door for Evan. The other teen sat down. “I threw up on your shirt,” Evan whined. Connor shrugged, “Small price to pay for a cute boyfriend.” He shut the door and hopped in the driver’s seat. “Besides,” he continued, “I got to wear one of yours and cuddle with you.”

Evan groaned, “I’ll never eat chipotle again.”

Connor laughed at that. “You were the one that didn’t want to go to Taco Bell,” he teased and squeezed Evan’s thigh. “Besides, it was funny watching all those stereotypical white girls lose their shit.”

Evan couldn’t help it, Connor’s smile was infectious. He buckled up and laid back against the seat. “So, where are we going?”

Connor was wearing a mischievous grin. “Picnic,” was all he said.

Evan raised an eyebrow, “Connor, it’s six o’clock. Why are we having a picnic?”

Connor just kept smiling and drove off.

Evan became lost in thought. He remembered how meeting Connor had been utterly terrifying. When you thought about it, it was really sad that the only person who would sign his cast was the guy who had pushed him. They had become friends after that and now… Evan saw the smile plastered on Connor’s face. He played with the hem of his shirt and thought of how he’d ask Connor. They had talked about sex before. Evan mostly stuttering before Connor finally told him to relax and that there was no rush.

_“Just tell me when you’re ready.”_

“We’re here,” Connor said and reached into the backseat to pull up a large blanket and a basket. “Come on.”

Evan grabbed his bag and got out. He didn’t recognize this place. “Where are we?” he asked, following Connor through the woods.

“Well, I was going to take you to that orchard but I thought we could use a change of scenery. I remember coming here as a kid, and that it wasn’t an official park so it didn’t really have a time limit.” Connor walked into the clearing and set down the basket. “Also, who the hell came up with time limits for parks, especially here? Trees don’t have to sleep and there aren’t really any wild animals around here, so why have them?”

Evan giggled at the passion in Connor’s voice. He always found his boyfriend’s random rants to be fun. He looked around. It was beautiful here. Dying sunlight was shining through the tree tops and littering the ground with scattered, golden light. “It’s wonderful,” he whispered. While it didn’t have a view like the orchard, it did have a sense of calm and security. Evan was so at peace that he didn’t even flinch when arms suddenly wrapped around him. Connor rested his chin on Evan’s shoulder.

“I knew you’d like it. Forest freak,” he teased and gave the other a kiss on the cheek.

Evan felt a shiver go up his spine. He tried to calm down before he ruined everything.  The teen covered Connor’s arms with his own. “It’s really nice. You used to come here?”

Connor nodded. “Yeah, before it all went to shit, I was really outdoorsy. I liked to run around and stuff, maybe that’s just part of being a kid though. You can always run, either from or to something.” Connor held Evan tighter. He didn’t want to think about himself, he just wanted the calm that Evan brought him. He always felt better when holding his Evangreen tree.

Evan frowned and decided to lighten the mood. “I’m disappointed I haven’t seen your baby pictures.”

That got a laugh from Connor. “I’ll show you mine if you show me yours,” he teased, whispering directly into Evan’s ear. He finally unwrapped himself from the other boy. “Come sit with me. I packed some snacks and shit.”

Evan sighed, trying to calm down. He should have masturbated today, maybe it would have helped with the overwhelming horniness he felt. “I don’t like shit,” he said to distract from his obvious arousal.

Connor feigned anger, “I’m getting tired of your sass, Hansen.”

Evan smiled brightly and moved to sit with his boyfriend. “You love my sass and my ass,” Evan shot back without thinking. His face flushed when he realized what he had said.

Connor was a bit shocked before looking Evan up and down. “Well, you’re not wrong.” That got a reaction. Evan covered his face with his hands and began mumbling to himself. Connor dug his nails into his palm. His boyfriend was too damn cute. He opened the basket. “I brought some Coke, candy, chips, junk food mostly.”

Evan smiled, calming down finally. “What kind of candy?”

  

* * *

 

 

An hour later and the pair were lying on the blanket and looking up at the stars. Evan had his head on Connor’s chest. He could hear the heartbeat under the jacket. Evan almost fell asleep because of the beat and gentle fingers that were running though his hair.

“I love you,” Connor whispered and kissed the cut locks.

Evan gripped at the grey jacket. “C-Connor, can I ask for s-something?”

Connor quirked an eyebrow. Evan only stuttered when he was nervous. “What is it?” he asked, careful with his tone.

Evan sucked in a breath. He could do this. All that practice wasn’t for nothing! “I-” he buried his face in Connor’s jacket. The smell calmed him. Earthy with a trace of weed and a hint of citrus. “I want to have sex,” he whispered.

Connor’s eyes widened. “What?” He obviously did not hear correctly.

Evan grit his teeth. “I want to have sex!” he yelled. Evan covered his mouth. His voice echoing through the trees and making him want to hide.

Connor sat up and Evan did the same. “You really want to?”

The shorter teen nodded. “Yeah, I really want to. I mean I want us to, I have but Idon’twantyoutothinkyouhavetoI-”

“Evan, calm down” Connor cupped his boyfriend’s face. “I really want to fuck you, so I need to know that you really want this because I’ve been thinking about it _a lot_.”

Evan licked his dry lips. That seemed to set Connor off. Evan gasped as he was pushed onto the blanket. Connor’s mouth was on his and Evan let himself relax into the embrace. They shifted so Connor was between his legs. Tongues and teeth were added to the kiss as curious hands began to wander. Evan shuddered as cold hands made their way under his shirt. Thin fingers pinched and pulled at his chest. Evan let his hands run under the layers Connor wore. The kiss grew sloppy as the two began to shimmy out of clothing. Evan’s shirt was tossed aside and his pants were being unbuttoned.

“Fuck,” Connor sucked in a shallow breath. He hovered over Evan, the sweet thing was panting. His gorgeous eyes were wide and his pupils were blown. Connor groaned. “I didn’t bring anything.”

Evan piped up and pointed to his bag, “I did! In the CVS bag, there’s stuff.”  

Connor grabbed the satchel and pulled out the plastic bag. He dumped it out on the blanket. Well then, at least Evan came prepared. “Oh,” was all he could manage to say though. 

Evan was covering his face.

Connor looked at his boyfriend. “So…why are there so many?”

“My mom didn’t know your size,” Evan said behind his hands.

“Really?” Connor asked, trying his hardest not to laugh. He looked at all the condoms. “I guess we should use all of them. Be a waste not to.”

That made Evan full on panic. “Some of them won’t fit you and that’s too much sex to be had on the first night and I don’t think I could ever do that much at once and-”

Connor was now laughing. “Evan, Evan, I’m kidding. Calm down,” he kissed the other. “You take everything so seriously, geez.” Connor sat back up and tied his hair into a messy bun. He grabbed one of the condoms, reading it in the moonlight before shrugging, it’ll work. Connor looked at Evan. “I’m guessing you want me to be naked too?”

“Please,” Evan begged, absolutely breathless.

Connor felt his dick twitch. He groaned, “Fine.” The teen unzipped his jacket and threw off his shirt. He knew Evan was staring at his scars. “I know, I look like a fucking train wreck.” Evan didn’t seem disgusted though. In fact, the other teen seemed mesmerized.

Evan reached out a hand to touch Connor’s chest. He traced a couple scars before moving up to his shoulder and trailed down the scarred arm. They were all healed, which meant Connor hadn't  hurt himself in a while. This made Evan swell with pride. Connor wasn’t hurting himself, Evan was helping him. “I love trains,” he replied, pressing a kiss onto the scarred wrist, “even the wrecked ones.”   

Connor felt the tears welling in his eyes. He tugged Evan closer to kiss him. “I fucking love you,” he whispered and began to scatter kisses all over his lover’s face. Connor pressed the other boy into the blanket.

Evan smiled into the kiss. The world seemed to quiet around them. Connor’s chest was warm against his and, for once, the physical contact made him feel confident instead of nervous. His hands wandered up the pale sides, trailing over his boyfriend’s ribs and scars. Connor’s hands were busy as well. One was keeping him elevated while the other was sliding into Evan’s khaki’s. Connor had, had sex before so he knew what he was doing. Evan let himself be led through it. “Connor,” he moaned. The pale teen was giving his cock slow strokes and it was torturous. “Please,” he whined.

Connor pulled away. He grabbed Evan’s pants. “Lift your hips,” he instructed. Connor stripped Evan of his pants and boxers. Right now Connor couldn’t think of any poetic or sappy bullshit to describe Evan Hansen naked, all he could do was let out a deep, “Fuck.” He moved between Evan’s thighs again. His boyfriend’s face was scarlet and his lips were red from their kissing. Those eyes though. They were gazing up at Connor like he was the most important thing in the world. “So fucking cute,” he mumbled and moved to steal another kiss.

Evan groaned at the feeling of Connor’s jeans against his skin. He grabbed one of the belt loops and tugged. “Off,” he growled, surprising the other boy.

Connor chuckled, “Who knew being horny made you grow a backbone.” He undid and pulled off his pants. “Do you want to keep kissing or…”

Evan looked away. His anxiety returning full force. “I-I don’t kn-know I-” Connor turned his head to face him. God Connor looked hot with his hair up. Evan let Connor thread their hands together. He gulped and squirmed a bit. “I’m sorry,” he whispered. He was at a complete loss about what they were supposed to do. Connor seemed to be examining him. Checking every tic and twitch.

“We don’t have to.”

“No!” Evan yelled, shocking both himself and Connor. He quickly explained, “I really want to, I just. I’ve never done this before and I’m kind of scared that I’m going to screw this up andthenyou’llhateme-”

“Evan.”

Said teen felt how Connor squeezed his hand. He took in a deep breath and relaxed. “I don’t want to mess up.”

Connor chuckled, “You’re going to. Hell, I’m going to, but that’s okay. First times are always awkward. Not like our first date awkward, but awkward.”

Evan giggled at that. He reached up and caressed Connor’s face. “I like being awkward with you.” Evan reached over and grabbed the lube. “So do I, or you, or… how does this work?”  

Connor took the bottle. “I’ll do it, this time. Next time I demand a show though.”

Evan sputtered out, “What do you mean a show?!”

Connor squirted some lube ono his fingers and warmed it up. “I mean, I want you to finger yourself for me.”

Evan didn’t really reply, mostly stammered out noises from the suggestion.

The boy was too tense, “Evan.”

“Yes?”

“What’s your favorite color?” Connor asked.

Evan scrunched his nose. “You know that it’s blue so AH-” His body went rigid and one of Connor’s finger sank into him. “What the hell, Connor?!”

The taller shrugged. “You were too anxious, thought I’d distract you.” He slowly pumped his digit in and out of Evan. Connor could hear the little gasps and shaky breaths his boyfriend was letting out. “Spread your legs more.” He pushed one of the plush thighs back.

Evan groaned but did as instructed. The finger inside him was moving and pressing around. A second joined the other and made Evan shudder. “Oh God.”

“Have you done this before?” Connor asked, mostly to keep the teen’s mind preoccupied.

Evan nodded. “Only a little bit,” he admitted, “I wanted to be ready for when we did this.” He noticed the light flush on Connor’s cheeks. His eyes drifted downward and saw how hard Connor was. Was that because of him? Evan felt a sense of pride, Connor found him attractive enough to get turned on.

Connor tried to bat away the image of his shy and sweet Evan fingering himself while thinking about them having sex. He scissored his finger and watched how Evan’s back arched. “Tell me if I’m going too fast.”

Evan shook his head, “No, you’re perfect.”

Connor pushed in another finger. He moved all three, curling, pumping, and twisting them inside his little tree. “God dammit, I really want to fuck you,” he thought aloud.

“Do it,” Evan begged. He wanted to know what it felt like to be screwed senseless. “Please fuck me.”

“You can’t… it’s not fair if you’re cute and sexy,” Connor growled. He pulled his fingers out and wiped them on the blanket. The teen tore open the condom wrapper and rolled the latex over his dick. He rubbed some lube on himself before tugging Evans hips, sliding the teen toward him. “Ready?”

“Please, please Connor,” Evan whispered.

Connor slowly pushed into the other and got the head inside. He cursed when Evan tightened. “You, you can’t tense up,” he reached down and gave Evan a few strokes. He felt the walls relax and sank in a few more inches.

“Hurts,” Evan whined. His eyes were shut tightly as his body was invaded.

Connor stilled. “I know,” it felt like pure agony but he waited for Evan to give him the okay to move. He saw those gorgeous eyes finally look at him. Evan gave him a little nod and he sunk in the rest of the way. Both teens sighed at the feeling. “Fuck Evan, so good,” he groaned. His hands dug into his tree’s hips.

Evan was shaking, but his legs were wrapped tightly around Connor’s waist. “Move,” he urged, “please fucking move.”

Connor didn’t need to be asked twice. He slowly bucked his hips. The sight of Evan under him, along with the little moans his tree was letting out, made had his dick hardening more. The urge to ravish the other boy was quelled though. He needed to be slow. He needed to be gentle. Evan wasn’t ready for that yet and Connor needed to be patient. At least, that’s what he thought. His boyfriend had other plans though.

Evan gripped at the blanket. “Harder,” he ordered, “Fuck me harder.” He saw the shocked look Connor was giving him. Horny and frustrated, he growled, “Fuck me like you mean it. I don’t want to be able to walk, or talk, or even think. So put that dick to good use.”

So Evan cursed and demanded things when he was horny. Connor filed that tidbit of information away before doing what his lover requested. He pushed the thighs farther apart before thrusting forward, driving himself harder and deeper in his lover. “Damn Evan, if I knew this was how I could get you to curse, I would have done it sooner.” He shifted his hips a bit.

Evan moaned loudly at the feeling. “Ah! You’re hitting it, wait, you’re hitting it!” His back arched. “Fuck, fuck, fuck!” Evan grabbed Connor’s shoulders. One of his hands moved to grab at Connor’s hair.

The teen hissed at the tugging on his hair and bucked his hips harder into the other. “God dammit, Evan!”

Evan raked his nails across Connor’s back. “Come on, come on!” He loved how messy and out of place Connor’s hair was, it framed his face and fell in such an erratic but beautiful way. “You’re so hot. God this feels so good!”

Connor groaned in agreement. He pulled away and out of the other.

Evan yelped in surprise as he was turned over onto his stomach. “Connor?” Evan’s question was cut short from Connor thrusting back into him. He moaned deeply at the feeling. The pace started up again and while Evan wanted to see Connor’s face, this new position felt amazing.

“What happened to that dirty mouth, Hansen?” Connor teased. He wished Evan’s hair was longer so he could grab it. Connor settled for his hips. He watched himself enter and leave the other. How Evan’s ass would bounce with each thrust. “So good,” he moaned.

Evan fell to his elbows. He tried to move back with Connor’s brutal pace but couldn’t keep up with the harsh rhythm. “Need,” he panted loud, “I need-” his words turned into sultry moans. A hand pushed him down into the blanket. Evan whimpered and reached between his legs to grab his hard cock. His hands worked on the length.

Connor could feel Evan tightening around his. “I’m gonna cum,” he groaned, “fuck I’m gonna cum.”

Evan came. His hand coated in his essence that dripped onto the blanket.

Connor groaned. Evan had gotten so tight. He growled, nails raking Evans unscarred skin. He let himself orgasm as well. They both basked in the afterglow as they came down from their highs. “I love you, Evan,” Connor whispered, planting kisses along the other boy’s spine.

Evan was a bit too spaced out to articulate a reply. He simply hummed back.

 

* * *

 

 

The drive back to Evan’s was short. There had been barely any traffic and with how Connor sped, it didn’t take long. The two tiredly stumbled into Evan’s home. They showered and collapsed onto Evan’s bed.

Both decided to wear only boxers and cuddled for warmth.

Evan listened to Connor’s heartbeat. “So,” he began, “we’re going to do that again right?” His boyfriend chuckled, “You bet your cute little ass we’re doing that again.” Evan giggled and snuggled closer to his lover. “I love you Connor Murphy.”

Connor was half asleep but whispered, “I love you too, Evangreen.”


End file.
